Synthesis of New Type Low Bandgap Anthracene Polymer and Investigation of Photonic and Electronic Properties
Sema Vural a, Ahmed Iraqi b
a Necmettin Erbakan Univ., Seydisehir Engineering Faculty, KONYA, 42360, Turkey
b University of Sheffield, Hounsfield Road, United Kingdom
International Conference on Hybrid and Organic Photovoltaics
Proceedings of International Conference on Hybrid and Organic Photovoltaics (HOPV16)
Swansea, United Kingdom, 2016 June 29th - July 1st
Organizers: James Durrant, Henry Snaith and David Worsley
Poster, Sema Vural, 205
Publication date: 28th March 2016

The identification of new organic semiconducting molecules has been a crucial factor driving improvements in organic thin-film transistors (OTFTs) and great achievements have been reported.1 Recently, there has been increased interest in the stability and processability of OTFT devices, in addition to the conventional focus on device performances. Organic molecules soluble in organic solvents are promising materials for inexpensive device fabrication since they can be processed by simple solution techniques such as spincoating, drop-casting, or inkjet-printing.2 To date, most efforts to synthesize soluble semiconducting molecules have focused on polymeric conjugated systems.3 Among the soluble oligomers reported to date, the functionalized pentacene has one of the greatest potentials as a semiconducting material.4 Adding bulky triisopropylsilylethynyl (TIPS) groups at the 6,13-positions of the pentacene not only improves the π-orbital overlap but also enhances the solubility and the oxidative stability of the material. Moreover, solution-deposited OTFT device properties with use of functionalized pentacene and anthradithiophene were reported.

In this study, new soluble anthracene derivatives containing thienopyrroledione (TPD) derivatives were synthesized via well-known synthetic routes. TIPS derivatives were added at the 9,10-positions of anthracene for the solubility and crystallinity. Structural characterization was achieved using 1H and 13C NMR, MS techniques. Molecular weight and polydispersity index were determined via GPC analysis. Thermal properties were determined using TGA and DSC analysis. The optical properties of all polymers were investigated by UV-Vis absorption spectroscopy on dilute chloroform solutions and The HOMO and LUMO energy levels (vs. vacuum) of the polymers were determined from the onsets of oxidation and reduction. The onsets were determined via cyclic voltammetry measurements, which were conducted on drop-cast polymer films in acetonitrile with tetrabutylammonium perchlorate as the electrolyte. As a result, the soluble anthracene core (TIPSAnt) is a potential precursor for the synthesis of novel semiconducting materials.

1. (a) Li, Y.; et all. AdV. Mater. 2006, 18, 3029. (b) Mcculloch, I. et all.; Nat. Mater. 2006, 5, 328. (c) Takimiya, K.; et all. J. Am. Chem. Soc. 2006, 128, 12604.

2.(a) Kraft, A.; et all. Angew. Chem., Int. Ed. 1998, 37, 402. (b) Murphy, A. R et all. J. Am. Chem. Soc. 2004, 126, 1596.       

3. (a) Shim, H.-K.; Jin J. I. AdV. Polym. Sci. 2002, 158, 1942. (b) Kim,Y. M.; et all Macromolecules 2006, 39, 4081.      

 4. (a) Anthony, J. E.; et all Org. Lett. 2002, 4, 15. (b) Sheraw, C. D. et all AdV. Mater. 2003, 15, 2009.



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